Authentic relationships between students and educators are important in the process of learning. Building these relationships with disengaged or at-risk students can be difficult at best. This monograph presents an overview of an approach to building authentic relationships based on the experience, insights, and educational background of the author, who is both a principal and a clinical social worker. Building trust as a means to building relationships is presented as the base of this approach. The theory behind it and the five essential strategies to building trust are presented with supplementary resources.